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While existing work assumes static, non-learning observers, real-world adversaries-such as in critical goods transportation or military operations-can adapt by learning from historical trajectories. To address this gap, we introduce Repeated Deceptive Path Planning (RDPP), a new formulation that explicitly models learnable observers. We show that existing DPP methods fail under this setting, as they cannot adapt to evolving adversarial predictions. While incorporating observer previous predictions into updates enables some adaptation, such incremental updates cause accumulative lag that degrades deception. 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